Showing 47 Vacation Rentals from Chestertown, MD

Amenities:
Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Coffee Maker, Computer Access, Dishes, Dishwasher, Filtered water, Internet Access, Iron, Ironing Board, Lakefront, Laundry, Linens, No Pets, Non-Smoking, Oceanfront, Pets OK, Refrigerator, Towels

Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Hunting, Restaurants, Swimming

Vacation Home Description:
description:Fairlee Point offers all the amenities of home plus great views, waterfront living, and a dock for your boat. If you've never been to the Eastern Shore you're in for a treat. Vacations are about getting away from it all - whether for a few weeks in the summer or a weekend get away. Fairlee Point offers both. Fall, Winter, Spring & Summer are each unique in its own way. Fall has wonderful colors, hunting, and watching the Canada Geese arrive for the winter. Winter is a time to curl up with a good book (we h... ;

Amenities:
Air Conditioning, Alarm Clock, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Freezer, Full kitchen, Garage, Internet Access, Iron, Lakefront, Laundry, Microwave, Non-Smoking, Oceanfront, Oven, Patio, Phone, Refrigerator, Screened porch, Stereo, TV, Toaster, VCR

Activities:
Beach, Biking, Boating, Fishing, Golf, Hiking, Horseback Riding, Hunting, Restaurants, Shopping, Water Skiing

Vacation Home Description:
description:Fairlee Point offers all the comforts of home with the beautiful and relaxing environment of the Eastern Shore of Chesapeake Bay. It is situated on a bluff overlooking Fairlee Creek with a private dock and 3.5 acres of private land. Enjoy the house, the grounds and the water in your private piece of heaven. In addition to the Great Room overlooking the bay there is a 1200 sq ft deck and a screened porch. Summer, winter, fall or spring, Fairlee Point is the place to be when it is time to get off the wor... ;

Amenities:
Air Conditioning, Balcony, Cable/Satellite TV, Fireplace, Internet Access, Iron, Non-Smoking, Oceanfront, Patio, Phone, Screened porch, Stereo, Swimming Pool, TV

Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Hunting, Sailing, Shopping, Swimming, Tennis

Vacation Bed & Breakfast Description:
description:Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century county-style estate rests on the waterfront of the Chesapeake Bay. With 12 questrooms, Great Oak offers the finest in a luxury bed and breakfast. Enjoy the most beautiful sunsets on the Eastern Shore from our private beach or our vast 12 acres of manicured lawns. As featured on The Today Show with travel editor Peter Greenberg, July 2005, and also featured in the February 2004 issue of Southern Living Magazine, in The Washingtonian 'Dream Weekends', April 2003, in Baltimore Magazine July 2003 'Bay Watch', in Chesapeake Life June 2003 issue, in Chesapeake Life 1999 winter edition 'Great Gatsby on the Chesapeake'. Recognized by American Historic Inns as one of their 'Top Ten Most Romantic Inns' for 2000. Approved by the Maryland Bed and Breakfast Association. Featured in Karen Brown's Travel Guide. Come for a getaway to Great Oak, a Chesapeake Bay Maryland bed and breakfast where the only honking comes from the geese, where the closest highway is the duck flyway, and where the only traffic you see from your room are the boaters sailing the crystal water of the Chesapeake Bay Waterfront just 200 yards away. Great Oak Manor, a Chesapeake Bay bed and breakfast, offers a private and secluded setting on the Chesapeake Bay for that 'get-a-way from it all' feeling in a magnificent 1700's style country estate with 12 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Each guest room of our Chesapeake Bay Bed and Breakfast is unique - from the grand Marmaduke Chesapeake Bay waterside room at the top of the spiral staircase to quaint sloped ceiling rooms on the third floor. Each individually air conditioned and each with its own story to tell. The Bed and Breakfast Innfeatures an expansive terrace offering exquisite views of the Chesapeake Bay. Lounge chairs are provided for those who wish to cozy up with a book or to just sit and watch the sunset. Great Oak Manor... ;

Amenities:
Air Conditioning, Alarm Clock, CD Player, Ceiling fans, DVD Player, Fireplace, Hot Tub, Internet Access, Ironing Board, Non-Smoking, Phone, Refrigerator, TV, VCR, Wireless Internet Access

Activities:
Beach, Bird watching, Board Games, Boating, Canoeing, Fishing, Horseback Riding, Hunting, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Tennis

Vacation Bed & Breakfast Description:
description:The Brampton Bed and Breakfast Inn is the Eastern Shore’s romantic oasis. Located on 25 wooded and landscaped acres, one mile outside the charming town of Chestertown, Maryland, Brampton beautifully blends the grand elegance of a historical estate with the comfort and amenities today’s travelers demand. Ignite or rekindle romance in a spacious, private and well-appointed guest room or cottage, offering wood-burning fireplaces, whirlpool tubs and glorious views. Enjoy a full breakfast graciously served at individual tables in Brampton’s beautiful dining room. Afternoon tea features delectable treats. Attention to detail, personal service, and friendly innkeepers will make your visit a memorable one. Chestertown is a colonial village with abundant activities, unique shops and great restaurants. It serves as a perfect base for exploring all that the Eastern Shore has to offer. Brampton Inn was the only Maryland property selected by National Geographic Traveler for it’s first-ever, annual “Stay List”. The editor’s list, which debuted in April 2008, includes just 150 properties in the United States, Canada, and the Caribbean.St. Michaels and Annapolis are an easy one-hour drive from the inn.;

Amenities:
Phone

Activities:
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Vacation Bed & Breakfast Description:
description:This pristine 18th-century manor house sits as a jewel on 10 acres overlooking Stoneybrook Pond. The six guest rooms, with parlors and numerous fireplaces, provide a casual and friendly atmosphere. Handsome polished wide-board floors add to the colonial decor. The Inn at Mitchell House is a popular setting for romantic weddings, small corporate meetings and other events. We will assist you in all of your organizational needs. Rates for the rooms include a full country breakfast, based upon two guests per room.;

Amenities:
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Activities:
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Vacation Bed & Breakfast Description:
description:The White Swan Tavern has been a familiar landmark in Chestertown since pre-Revolutionary War days. Not far from the great Eastern cities, it is an unexpectedly quiet, elegant place nestled in the history of Maryland''s Eastern Shore. The White Swan is for those who treasure serene streets, birdsong mornings, impeccable service, and the grace of New World Tradition.;

Amenities:
Phone

Activities:
Hunting

Vacation Bed & Breakfast Description:
description:We are committed to providing our guests with the best we have to offer, surpassing guest expectations. Unwind and relax at this respectable 28-room Inn, conveniently located in peaceful Chestertown, a historic colonial town by the sparkling waters of the Chester River. ;

Amenities:
Phone

Activities:
Hunting, Sailing, Shopping

Vacation Bed & Breakfast Description:
description:Much like the heritage of the Claddaugh ring, the Claddaugh Farm Bed and Breakfast is steeped in tradition as well. Nestled midst gentle Queen Anne's county farmlands, this stately turn-of-the-century farmhouse is an inviting stop for Eastern Shore Travelers. During your stay, you'll be tempted to spend your time sailing along the historic Chestertown water-front, hunting in the amply stocked Maryland game lands, shopping at many quaint collectible shops around town, or relaxing with a book on a leisurely conversation in the parlor by a warming fire. Parlor Front Porch We extend a gracious invitation to come and enjoy our home and all that the area has to offer.;

Amenities:
Air Conditioning, Cable/Satellite TV, Ceiling fans, DVD Player, Fireplace, Garage, Hot Tub, Kitchenette, Laundry, Linens, Pets OK, Phone, Refrigerator, Room Service, Smoking OK, Stereo, Swimming Pool, Towels

Activities:
Beach, Biking, Boating, Diving, Fishing, Golf, Horseback Riding, Movie Theaters, Restaurants, Shopping, Sightseeing, Snow Skiing, Surfing, Swimming

Vacation Bed & Breakfast Description:
description:Brampton Bed And Break is a 1 bed 1 bath Inner City Guesthouse Vacation Rental located in United States's Chestertown Maryland. ;

Amenities:
Air Conditioning, Alarm Clock, Cable/Satellite TV, Ceiling fans, Fireplace, Garage, Hot Tub, Kitchenette, Laundry, Linens, Pets OK, Phone, Refrigerator, Room Service, Smoking OK, Stereo, Swimming Pool, Towels

Activities:
Beach, Biking, Golf, Horseback Riding, Movie Theaters, Restaurants, Sailing, Shopping, Sightseeing, Snow Skiing, Swimming

Vacation Bed & Breakfast Description:
description:Great Oak Manor is a 1 bed 1 bath Suburban Guesthouse Vacation Rental located in United States's Chestertown Maryland. ;

Amenities:
Air Conditioning, CD Player, Ceiling fans, Computer Access, DVD Player, Fireplace, Hot Tub, Internet Access, Iron, Ironing Board, Laundry, Non-Smoking, Phone, Stereo, Swimming Pool, TV, VCR, Wireless Internet Access

Activities:
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Massage, Museums, Restaurants, Shopping, Swimming, Tennis, Watersports

Vacation Bed & Breakfast Description:
description:This property has been featured in Southern Living, Philadelphia, Diversions, Road Best Traveled, Washingtonian, Country Inns, New Choices, Chesapeake Life, Time Magazine., Today Show with Peter Greenberg, July 2005. ;

Amenities:
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR, Wireless Internet Access

Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Snow Skiing, Swimming, Tennis, Watersports

Vacation Bed & Breakfast Description:
description:Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that get-a-way from it all feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and... ;

Amenities:
Air Conditioning, Alarm Clock, Fireplace, Hot Tub, Internet Access, Ironing Board, Jacuzzi, Non-Smoking, Pets OK, Phone, Refrigerator, TV, VCR, Wireless Internet Access

Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports

Vacation Bed & Breakfast Description:
description:You can swing on the comfy porch swings and enjoy a cool breeze while sipping ice tea or lemonade. From this quiet spot observe the flight and hear the songs of Brampton's numerous birds. Swallows, gold finches, cardinals, hummingbirds, herons, egrets, Canada geese, wood ducks, woodpeckers, owls, blue birds, Baltimore orioles, and many other birds have been spotted on this property. ;

Amenities:
Air Conditioning, Fireplace, Hot Tub, Internet Access, Iron, Ironing Board, Laundry, Non-Smoking, Phone, Refrigerator, TV, Wireless Internet Access

Activities:
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Museums, Shopping, Tennis, Watersports, Yoga

Vacation Bed & Breakfast Description:
description:This property has 6 total guest accommodations with private bath, 2 total suites, including 1 two-bedroom suite and 2 conference rooms. The types of beds available include King, Queen, Twin and Double. ;

Amenities:
Air Conditioning, Cable/Satellite TV, Computer Access, DVD Player, Fireplace, Hot Tub, Iron, Ironing Board, Laundry, Non-Smoking, Phone, Refrigerator, TV, VCR, Wireless Internet Access

Activities:
Beach, Canoeing, Fishing, Golf, Hiking, Kayaking, Museums, Shopping, Tennis, Watersports

Vacation Bed & Breakfast Description:
description:This property has been featured in Washingtonian, New York Magazine, Glamour, Philadelphia Inquirer, Baltimore Sun, Kent County News, Ten Best Inns in the Country, New York Times, Washington Post, National Geographic Traveler. ;